


Richie Gets Jealous and Regrets It

by acefusti138, trxshmxxth



Series: Now THAT’S What I Call Painful Headcannons! [1]
Category: IT (2017), IT - Stephen King
Genre: A LOT of Angst, Angst, Bottom Richie mentioned, Dysphoria, Eddie has to care for his boyfriend, Established Relationship, HAVING A GOOD TIME, Hurt/Comfort, I shouldn’t have access to a computer to write this shit, M/M, Original Character - Freeform, Panic Attacks, Planned Pregnancy, Psychological Trauma, References to Homophobia, References to Transphobia, Richie has to care for his boyfriend, Richie’s gets jealous and prositutes himself for a very short time to his teachers, Slut Shaming, Suicical Thoughts, The loser’s Club, Trans Male Character, Trans Male Pregnancy, Trans!Eddie Kaspbrak, Transphobia, also the underage is also related to the teacher fucking Richie, but here I am anyways, each chapter is a different set of headcannons in differently universes unless stated otherwise, giving Reddie pain, it’s just a lot of headcannons so tags will be added as I go on, listen man it’s some dark shit, me and Oliver just love to hurt our sons, might actually just make it a series lmao, no pennywise, pregnacy, references to self harm, self harm mentioned, the rape/non-con is only briefly mentioned when the teacher fucks Richie, the slut shaming is also only briefly mentioned, then traumatized by his actions, transphobic slurs not used but mentioned, use of a safe word
Language: English
Status: Completed
Published: 2017-12-22
Updated: 2017-12-22
Packaged: 2019-02-18 12:46:28
Rating: Mature
Warnings: Rape/Non-Con, Underage
Chapters: 1
Words: 2,752
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13100415
Author URL: https://archiveofourown.org/users/acefusti138/pseuds/acefusti138, https://archiveofourown.org/users/trxshmxxth/pseuds/trxshmxxth
Summary: Headcannon Time! Prompt:Eddie has a boyfriend that isn’t Richie and Richie gets jealous. Ends up doing something he regrets and he and Eddie get to deal with the Drama.





	Richie Gets Jealous and Regrets It

**Author's Note:**

> what up. i’m Alive. out here, bringing pain and angst to the wonderful ship of reddie that stephen king would be proud of iF HE HADN’T FUCKING KILLED OFF MY BABY BOY! enjoy :)

Richie would be the coldest and most jealous asshole if Eddie dated literally anyone else. He'd physically go out of his way to avoid him mostly just to avoid his own distress without even considering the feelings of his best friend. Like he's literally late to a shared class with Eddie because he takes the long way to avoid Eddie. Leaves class the same way to avoid them both. He doesn't like to talk to him at all. Not even texts or written.

Eddie slides Richie a note in class and he looks at it, glances at Eddie, and just tears it into little pieces that he flicks at people to distract himself. It’s tearing them both down and they just drift apart slightly until the day Eddie splits with his boyfriend in Sophmore year.

By then, Richie's talking to him but not like before. No late night ramblings about the silliest things, no existentialism, no ranting about shitty parents, nothing. But Eddie immediately goes to Richie all upset and he's literally like the old Richie, holding him and telling him it was probably the best because he was an ass. The usual stuff a friend tells you.

Bonus if Richie's constantly absent from school but somehow managing better grades than usual. Why? You can do a lot more than extra credit to get on a teacher's good side. Besides, it helps distract him, even if its only for a little while, and sometimes makes him feel better when he feels especially like garbage.

Sure, Richie might not be a virgin, but the first time with Eddie is like he is, and it's like he's not sure what to do with such a softboi that he would hate to hurt. Eddie is happy to guide him around and tells him what he likes that Richie does and what doesn't do it for him. Its slow and tender and they just take the time to enjoy each other's bodies and really enjoy the sex.

I've always imagined that if Richie didn't lose his V card to Eddie it would have probably been to Bev because they're both teens and experimenting with stuff. Bev becomes a lesbian and the two have that inside joke that Richie turned her gay. Not to toot Stephen King's horn but something like that would probably make Bev and Richie a lot closer. Richie learns some girl anatomy, Bev learns she doesn't like dudes. Win-win probably.

Richie will just skip the class he has with Eddie and keep his grade up, it’s a younger teacher, mid 20’s and a pretty attractive guy, he offers weed and sex and the guy accepts it. Richie was never super into it, sure it was a nice fuck and he realized he hated bottoming when the guy on top of you doesn’t even fucking prep you, he’s usually high anyways to forget, but once Eddie comes in after school to grab a textbook he forgot, Richie is high and the room smells like weed and Richie is getting banged over the desk with tears streaming down his cheeks, he’s biting into his forearms and Eddie can hear his name being whimpered out from Richie.

He bolts out of the room before the teacher even notices, but he texts Richie that night incredibly confused and hurt, ‘Richie you went for the teacher?’ and other things, he doesn’t get a single response and his relationship with his boyfriend has been shit since Richie began to ignore him.

The day Richie tore up the note, Eddie had gone to his boyfriend in tears, and once Eddie explained what Richie had done the guy got annoyed. It was lays about Richie with Eddie, and finally the guy had enough. They had a huge fight and finally the guy just goes  
“If you love this Richie guy so much why don’t you go fuck him! Date him instead!”

They break up.

Eddie texts Richie again what’s happening but Richie has been unconscious in his room. He had torn and had taken four painkillers to knock himself out and try to make the pain ease up. He knocks his leg really hard on his bike as an excuse for his awful limp, but when he checks his phone and sees 45 texts from Eddie and 5 calls from him, he panics.

When he gets to school, the losers are in their normal spot in the cafeteria, Eddie is sitting on the table as usual and Bev is consoling him with Stan, he’s crying and one of them sees Richie and gives him a _Look_. The one that says;

“He needs you. Fix this Richie because we tried to tell both of you to quit being dumbfucks.”

Richie goes over to Eddie and hugs him, Eddie cries in his arms and they all skip first period (they move instead to one of the storage closets the theater department uses right as the bell rings) and finally the other losers go to class, Richie and Eddie stay behind, Eddie is still upset and  
“ _Richie why the fuck wouldn’t you just talk to me?! You would rather whore yourself for our teacher so you could avoid me?! My ex wasn’t nearly that fucking important ‘Chee! You’re my best friend!_ ”

He’s crying and Richie feels his heart shatter because he did this to Eddie, he made him cry like this and he just holds Eddie close as he cries, he deserves the anger and finally Eddie grabs his cheeks and kisses him, they both taste like tears and Richie is still in a lot of pain, he had been torn good, but he holds Eddie for a while, talking to him about anything he can think of. For hours, just babbling and making up for lost time. They don’t announce that they’re dating for a year because Richie doesn’t want the teacher to target Eddie and Eddie don’t want any teachers finding out and moving their seats in class. Richie ends up rather traumatized by the tearing incident.

Now imagine trans Eddie. His ex boyfriend calls him slurs and outs him to the school. Eddie refused to have sex with him; the guy becomes a fuckin snake and tries to destroy Eddie, Eddie is a mental wreck and Richie comes into school that day with a paper on his locker saying ‘ _Missing: Edith Kaspbrak. Lost when she cut off all her hair and started calling herself Eddie_ ’ and Richie is furious.

He dedicates a week to just Eddie and making him feel better, apologizing. He holds shit over the teacher’s head until he and Eddie guarantee ace the class and he has whored himself to other teachers for grades, even offers himself to some of Eddie’s teachers because Eddie is going through enough right now.

It works, but one day Eddie realizes Richie comes over from school with bruises and bites all over him and he’s limping and  
“Richie what happened?” Richie has himself in a corner, the teachers want more from him and he’s stuck and scared and it takes a lot of effort from Eddie to get Richie out of that situation. By senior year they’re dating and Eddie has grown used to the transphobic things stuffed in his locker, Richie is indifferent to the notes of being called the school whore in his locker, they have each other and that’s all they need.

But it’s not sunshine and rainbows.

Richie’s beyond disgusted with himself, sometimes he’ll sit in the shower and scrub at his skin until it’s pink because he let his teacher touch him just because he was jealous of Eddie’s boyfriend. Of course Eddie feels awful and blames himself and it just makes Richie feel worse. Even now he’s hurting the love of his life and he knows Eddie walked in on him and saw him like that, he did it with so many faceless teachers and could have even ruined their lives, he feels like a disaster that only hurts people and constantly thinks he doesn’t deserve to be around.

Only constant therapy and support from Eddie and their friends keeps him from self harming and he’s had many relapses, Eddie just feels horrible about it and wishes he had never dated the guy, wishes he could go back in time and yell at himself to snap out of his refusal to admit he’s in love with his best friend, that he could show his past self the scars of his own self harm and some scars from when Richie panics and thinks he’s under a faceless teacher and clawing at himself to get out of his own skin, except Eddie tries to hold him and keep him from hurting himself and usually gets pretty scratched up in the process.

That some stupid fuckwad is never worth what Richie does to himself out of jealousy and that Richie will never be the same afterwards.

Richie and Eddie in college and barely supporting themselves because without therapy, Richie and Eddie are both absolute wrecks, most nights one of them is battling thoughts they don’t want and trying to comfort each other.

They’re just struggling to survive and it takes years and years.

I’m talking almost six years since the first incident of Richie whoring himself for the constant, mind-numbing feeling of guilt and disgust to stop encasing Richie whole for days on end.

It takes years for Eddie to feel remotely comfortable enough in his body to be able to look in the mirror and feel okay with who he is.

It takes years for Richie and Eddie to wake up and not have to apologize for a nightmare that the other inadvertently caused, and it takes years for them to feel comfortable enough to switch.

The first time Richie bottoms is almost 5 years from the last time he had bottomed, the day he had torn and Eddie had seen, and Eddie takes his time, takes almost an hour prepping Richie, soothing him that it’s okay, that their safe word is there and if Richie feels at all uncomfortable, to let him know, or if he feels Panic seizing up his throat to blink three times and wrinkle his nose, that if it hurts at all to tell Eddie to stop.

It’s a toy the first time. Richie is trying his best to stay calm, he _needs_ to prove to himself he can do this. He takes it well at first, Eddie’s tiny fingers prep him and he’s getting worked up, his cock is hard against his stomach, he’s leaking and  
“Eds, you can put it in, I’m ready,” and Eddie places the tip in slowly, Richie stiffens and he’s doing his best, “ _It’s fine— everything is fine– I’m fine— Eddie is right here—_ ” but then it’s all the way in and “ _Fuck I can’t do this— Eddie take it out– god take it out take it out! S-shit, silver, silver!_ ”

Eddie has it out within seconds, Richie is crying and it’s like he had never been hard, he can’t fucking do it, “Eddie I can’t, _I can’t do it—!_ ”

Eddie spends hours consoling him, stroking his hair and soothing him that “It’s okay, you did so good, I’m right here Rich, you’re safe. It’s over and we don’t have to do it again if you don’t want to, I’m so proud of you, it’s okay.” He’s proud of him, they have the therapist on call and if Richie feels like he’s going to relapse that Eddie is right there and everything is okay.

It takes almost a year for Richie to actually take the whole toy and cum without getting upset or panicked at some point, and another 6 months after that for him to take Eddie —trans!Eddie uses a strap on— and be okay. Eddie is incredibly patient, he’s so proud of Richie for doing so well and there’s many hours of aftercare every time.

Trans!Eddie one day whispers that he loves Richie more than anything and Richie whispers he loves him back, Eddie realizes Richie overcame this and that Eddie feels a growing need in the pit of his tummy to overcome something he’s always wanted.

When he was little, even when he knew he was a boy, he was curious about babies. He’s never had a sibling and babies adore him, with his calm nature and caring disposition. They were cute and sure— they burped and pooped and cried but so did his best friend! They were so tiny and cuddly and warm, they gave such cute little burbles and cooes and he just naturally did well with them.

His mother never wanted him around them, said he could get them sick if he wasn’t careful and a tiny voice inside of him wanted to do nothing more than prove her _wrong_ , that he could be a better sibling or even a better parent to a little baby when he grew up! He’d be the best Dad ever!

He met Richie at 7 and they were inseparable, now he’s almost 26 and they’re life is stable now, they both have steady jobs, a good condo in the downtown of New York, and he feels like he can handle it.

He whispers to Richie that he he wants to love more than just Richie and Richie looks confused and then Eddie points at his abdomen, Richie pieces it together and he looks elated, he whispers back that he would support Eddie every second of the way and that Eddie supported him, and that Richie would support him too.

It takes months for Eddie to feel comfortable having sex without a condom, luckily the birth control is wearing off so they have time to get used to it, they tested and Eddie is still fertile, he’s so nervous but finally after almost 3 months of trying, he feels sick and achy in the morning, sometimes gets sick.

“Richie I think we did it.” His next doctor’s appointment a week later confirms it and he’s happy but as expected his dysphoria is horrid, he knows he wanted this but he’s never felt more like his body isn’t his own, Richie supports him just as he promises.

In the end they have little Charlotte Renee Tozier, who has Richie’s freckles and Eddie’s little button nose.

Her pregnancy is one of the hardest things Eddie has ever done.

His final month is akin to Richie’s first time taking the toy. He constantly is incredibly uncomfortable.  
“Richie I can’t do it, I can’t— I don’t want to do this anymore! I just want her here, I can’t take it with her inside anymore!”

Richie takes a lot of time off work because Eddie is too anxious to go to work, his maternity leave started two weeks early after an early labor scare left him in bed rest, he still delivers at just barely nine months, little Charlie is so, so tiny, she just scrapes by being big enough to go home like normal babies, and Eddie’s postpartum mixed with dysphoria is a wreck.

He still loves Charlie more than anything but when the Losers see Eddie after the first week following her birth, he’s a literal zombie. He functions only enough to feed and care for her, then sleeps all day otherwise. Richie is home to take care of Charlie while Eddie sleeps and Eddie does his part as best he can but it’s clear he’s not OK. The Loser’s offer to take over for a day or two once a week, so Eddie can go to therapy and have Richie support him.

This goes on for almost three months; once a week the Loser’s take care of Charlie all day, and Eddie improves greatly. He starts yoga to lose the baby weight and combat the depression and dysphoria he feels. He goes on a lot of walks with Richie and Charlie, who’s in a sling at his chest.

The fresh air and exercise help.

Yeah, he still has days where he can’t get out of bed and throws up what he eats and can only function enough to take care of Charlie, but it’s met with incredible support.

Every time he tells Richie he doesn’t think he can handle it, that he’s a failure and that Charlie will hate him, Richie just reminds him that he had felt the same way and Eddie never ever gave up on him.

Richie won’t give up on him either.

 

**Author's Note:**

> this might be part of a headcannon series?? idk but anyways s/out to my boy Oliver, he helps me make this painful shit and gives me ideas so thanks man! kudos is loved but this shit hurts so if ya don’t, I feel ya B)


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